Midwest FurFest got its start as the furry track for Duckon, a Chicago-based science fiction convention. The furry track was started at Duckon 3 in 1994 and was headed up by Robert King. The track grew larger each year and it was estimated that by Duckon 8 (1999) between one-quarter and one-third of the attendees were there due to interest in the furry track.

The track ran into problems because it was running out of room to expand without costing other parts of Duckon programming space and time. It was decided that the best course of action was to spin off into a new convention.

Thus Midwest Furry Fandom, Inc. was created and Midwest FurFest was born, to take place in November 2000, on
the weekend before Thanksgiving. The parting was amicable, and Duckon lent a good bit of expertise and manpower to help make the first year of Midwest FurFest a success.

Since then, the convention has grown from 388 attendees in 2000 to 3,904 in 2013, making it the 2nd largest furry convention. It has raised over $192,125 for various charities.

The next year was a big jump for the convention, both in attendance and space as MFF moved a few miles south to the Hyatt Regency Woodfield in Schaumburg, Illinois. The new location was a huge hit among the 685 attendees, with its close proximity to Woodfield Mall, many restaurants, and other amenities. Jim Doolittle (aka Aureth) took the reins as convention chairman. Animals for Awareness was once again the chosen charity, and the charity auction and contributions at their table raised a total of $6,088. Programming continued to expand, assisted by Guests of Honor Ursula Husted, Ysengrin Blackpaw, and D.C. Simpson.

Aureth again chaired the convention in 2003, still at the Hyatt Woodfield. Thomas K. Dye, M.C.A. Hogarth, and DBruin were the Guests of Honor. The charity auction and donations to Animals for Awareness totaled $6,500 that year. 800 furry fans turned out that year, establishing a steady growth curve for the convention. At the end of the convention, Aureth followed the "two years and out" tradition established by Robert King and turned the reins over to Dan Hauschild (aka Takaza J. Wolf). Mary Jo Pehl of Mystery Science Theater 3000 appeared.

2004 was another banner year for MFF at the Hyatt Regency Woodfield, with 959 attendees. A new charity, Furry Friends Foundation, was the recipient of $7,000 raised by donations, the charity auction, and a unique, one-time-only joint show featuring Uncle Kage and 2 the Ranting Gryphon together on stage for almost two hours. The Guests of Honor that year were Ursula Vernon, ScribbleFox, and David Gilbert. This was the first year that MFF reached outside furry fandom for a Guest of Honor and Mr. Gilbert wrote afterwards that he had a fantastic time.

Gene Breshears, Tincrash, and Kenket were the Guests of Honor in 2005. The convention continued to grow, breaking the thousand-furry mark for the first time with 1,066 in attendance. Wildlife in Need, a small wildlife rehabilitation organization, was the recipient of $6,800 in donations. The highlight of the Charity Auction was the auctioning off of an evening with 2 and Uncle Kage entertaining the winner and their friends in a private performance; in the end, two groups who were bidding against each other pooled their funds and the performance went for $650. This was Takaza's last year heading the convention, as he passed the chairmanship over to Linnaeus for 2006. It was also announced that Midwest FurFest would be returning to the Hyatt Regency Woodfield in 2006.

Illustrator Heather "Kyoht" Luterman , fursuit designer Whitefox (aka Whiteyfawks) and artist and designer Spunky were the Guests of Honor in 2006. The theme was Midwest FurFest County Fair. 1,422 people were in attendance. Fursuit parade attendance was at 213 participants, a record at the time. The Charity Auction raised $5570 for the Safe Haven Wildlife Refuge, not including donations. $13,048.96 in all was raised for the refuge.

Linnaeus chaired the convention again, which took place November 16-18, 2007 at the Hyatt Regency Woodfield in Schaumburg, Illinois. The Guests of Honor included illustrator and artist Erika Rosengarten, artist and costumer Jill0r, and author Will Sanborn. The theme was Critters on the High Seas. Attendance was 1,689, and the fursuit parade had 286 participants. The convention raised more than $15,000 for Flint Creek Wildlife Rehabilitation.

Midwest FurFest was held from November 21st to November 23rd in 2008. Duncan da Husky was the convention chairman, and the convention moved to a new venue: The Westin Chicago North Shore in Wheeling, Illinois. The theme was North to Alaska.

Total attendance was 1,992, and over $15,000 was raised for their charity, Rainbow Animal Assisted Therapy. The Art Show generated $22,928 in revenue.

2,040 attended the 10th anniversary of MFF, to which all previous guests of honor were invited. No complaints were voiced at the feedback session, but art show sales also suffered from the economy, despite an increase in the number of pieces. An experimental theatrical event - Too Much Light Makes The Baby Go Blind - gained a positive reception, while $12,971 was raised for the charity KARE For Wildlife.

At closing, it was announced that the convention would move to the Hyatt Regency O'Hare in Rosemont, Illinois in 2010.

MFF 2010 was held on 19-21 November at the Hyatt Regency O'Hare in Rosemont, Illinois. The convention theme was Chicago Blues. Total attendance was 2,285, a 12% increase from 2009, and $11,300 was raised for the charity Castaway Pet Rescue, Inc.

Midwest FurFest 2011 took place November 18-20 at the Hyatt Regency O'Hare in Rosemont, Illinois. Theme for the convention was Route 66. Attendance figures were of 2,600, with 574 participants in the fursuit parade. $19,575 was raised for convention charity Lake County Animal Education and Rescue.

The 2012 Midwest FurFest took place the 16th-18th of November in Rosemont, Illinois at the Hyatt Regency O'Hare, with a theme of "It Came From TV". The attendance figure of 3,216 exceeded that of Further Confusion 2012, making it the second largest furry convention. 743 participated in the fursuit parade, and convention charity Felines & Canines Inc. took home more than $40,500.

Midwest FurFest 2013 was the 14th convention held again at the Hyatt Regency O'Hare in Rosemont, Illinois. The theme was "Pirates of Lake Michigan" and had a attendance figure of 3,904 at the closing ceremony. The 2013 convention raised more than $28,000 for the charity One Tail at a Time.
The convention took place on November 22-24.

The 2014 Midwest FurFest took place on December 5-7 at the Hyatt Regency O'Hare in Rosemont, Illinois and had the theme "Holidays in the City" with an attendance figure of 4571. The convention raised $31,150 for Critter Camp.